دورية أكاديمية
A concise synthesis of tetrodotoxin.
| العنوان: | A concise synthesis of tetrodotoxin. |
|---|---|
| المؤلفون: | Konrad DB; Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 Munich, Germany., Rühmann KP; Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003, USA., Ando H; Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University, Tokyo, Japan., Hetzler BE; Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003, USA., Strassner N; Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA., Houk KN; Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA., Matsuura BS; Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003, USA., Trauner D; Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003, USA. |
| المصدر: | Science (New York, N.Y.) [Science] 2022 Jul 22; Vol. 377 (6604), pp. 411-415. Date of Electronic Publication: 2022 Jul 21. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Association for the Advancement of Science Country of Publication: United States NLM ID: 0404511 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1095-9203 (Electronic) Linking ISSN: 00368075 NLM ISO Abbreviation: Science Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Original Publication: New York, N.Y. : [s.n.] 1880- |
| مواضيع طبية MeSH: | Tetrodotoxin*/chemical synthesis , Voltage-Gated Sodium Channel Blockers*/chemical synthesis, Catalysis ; Cycloaddition Reaction ; Guanidine/chemistry ; Ruthenium/chemistry ; Stereoisomerism |
| مستخلص: | Tetrodotoxin (TTX) is a neurotoxic natural product that is an indispensable probe in neuroscience, a biosynthetic and ecological enigma, and a celebrated target of synthetic chemistry. Here, we present a stereoselective synthesis of TTX that proceeds in 22 steps from a glucose derivative. The central cyclohexane ring of TTX and its α-tertiary amine moiety were established by the intramolecular 1,3-dipolar cycloaddition of a nitrile oxide, followed by alkynyl addition to the resultant isoxazoline. A ruthenium-catalyzed hydroxylactonization set the stage for the formation of the dioxa-adamantane core. Installation of the guanidine, oxidation of a primary alcohol, and a late-stage epimerization gave a mixture of TTX and anhydro-TTX. This synthetic approach could give ready access to biologically active derivatives. |
| المشرفين على المادة: | 0 (Voltage-Gated Sodium Channel Blockers) 4368-28-9 (Tetrodotoxin) 7UI0TKC3U5 (Ruthenium) JU58VJ6Y3B (Guanidine) |
| تواريخ الأحداث: | Date Created: 20220721 Date Completed: 20220725 Latest Revision: 20220805 |
| رمز التحديث: | 20221213 |
| DOI: | 10.1126/science.abn0571 |
| PMID: | 35862530 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1095-9203 |
|---|---|
| DOI: | 10.1126/science.abn0571 |